CA2146701A1 - Composes heterocycliques a activite anti-diabetique, leur preparation et leur usage - Google Patents

Composes heterocycliques a activite anti-diabetique, leur preparation et leur usage

Info

Publication number: CA2146701A1
Authority: CA; Canada
Prior art keywords: group; carbon atoms; substituted; substituents; unsubstituted
Prior art date: 1994-04-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002146701A

Other languages

English (en)

Inventor

Takashi Fujita

Koichi Fujimoto

Takao Yoshioka

Hiroaki Yanagisawa

Toshihiko Fujiwara

Hiroyoshi Horikoshi

Minoru Oguchi

Kunio Wada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sankyo Co Ltd

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-04-11

Filing date

1995-04-10

Publication date

1995-10-12

1995-04-10 Application filed by Individual filed Critical Individual

1995-10-12 Publication of CA2146701A1 publication Critical patent/CA2146701A1/fr

Status Abandoned legal-status Critical Current

Links

230000003178 anti-diabetic effect Effects 0.000 title abstract description 4
238000002360 preparation method Methods 0.000 title description 201
150000002391 heterocyclic compounds Chemical class 0.000 title description 3
-1 azaindolinyl Chemical group 0.000 claims abstract description 717
150000001875 compounds Chemical class 0.000 claims abstract description 384
125000003277 amino group Chemical group 0.000 claims abstract description 121
125000000217 alkyl group Chemical group 0.000 claims abstract description 111
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 104
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 63
125000003545 alkoxy group Chemical group 0.000 claims abstract description 58
125000005843 halogen group Chemical group 0.000 claims abstract description 58
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 40
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 40
125000005945 imidazopyridyl group Chemical group 0.000 claims abstract description 29
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims abstract description 25
125000001041 indolyl group Chemical group 0.000 claims abstract description 20
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
239000001301 oxygen Substances 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 296
239000000203 mixture Substances 0.000 claims description 266
229910052705 radium Inorganic materials 0.000 claims description 181
229910052701 rubidium Inorganic materials 0.000 claims description 181
125000003118 aryl group Chemical group 0.000 claims description 167
125000001424 substituent group Chemical group 0.000 claims description 167
238000000034 method Methods 0.000 claims description 158
125000002252 acyl group Chemical group 0.000 claims description 98
125000001931 aliphatic group Chemical group 0.000 claims description 79
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 61
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
229910003827 NRaRb Inorganic materials 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 31
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 27
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
125000004414 alkyl thio group Chemical group 0.000 claims description 24
125000001589 carboacyl group Chemical group 0.000 claims description 21
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
125000004430 oxygen atom Chemical group O* 0.000 claims description 21
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 17
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 5
201000005577 familial hyperlipidemia Diseases 0.000 claims description 5
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
238000011321 prophylaxis Methods 0.000 claims description 5
VPFJHPSVNYPBHL-UHFFFAOYSA-N 5-[[4-[(5-methoxy-3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C2=NC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O VPFJHPSVNYPBHL-UHFFFAOYSA-N 0.000 claims description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 4
VJRCELWLZGOZTR-UHFFFAOYSA-N 5-[[4-[(3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CN=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O VJRCELWLZGOZTR-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
NYZCYOCLLSTCPQ-UHFFFAOYSA-N 5-[[4-[(3-methyl-5-propan-2-yloxyimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C2=NC(OC(C)C)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O NYZCYOCLLSTCPQ-UHFFFAOYSA-N 0.000 claims 3
RGQNYGHRASYZHL-UHFFFAOYSA-N 5-[[4-[(5-chloro-3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(Cl)N=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O RGQNYGHRASYZHL-UHFFFAOYSA-N 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 2
WEEPXEIATGBQQK-UHFFFAOYSA-N 5-[[4-[(3-methyl-5-oxo-4h-imidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(O)N=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O WEEPXEIATGBQQK-UHFFFAOYSA-N 0.000 claims 1
BHNIQYLHLZTUAN-UHFFFAOYSA-N 5-[[4-[(5-ethoxy-3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C2=NC(OCC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O BHNIQYLHLZTUAN-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000002218 hypoglycaemic effect Effects 0.000 abstract description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 559
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 306
238000006243 chemical reaction Methods 0.000 description 168
239000002904 solvent Substances 0.000 description 153
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 138
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 130
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 117
239000000741 silica gel Substances 0.000 description 113
229910002027 silica gel Inorganic materials 0.000 description 113
238000002844 melting Methods 0.000 description 111
230000008018 melting Effects 0.000 description 111
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
239000012043 crude product Substances 0.000 description 87
239000003480 eluent Substances 0.000 description 82
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 78
238000004440 column chromatography Methods 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 65
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
238000004821 distillation Methods 0.000 description 51
239000000047 product Substances 0.000 description 51
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000003153 chemical reaction reagent Substances 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
239000000460 chlorine Substances 0.000 description 44
239000000243 solution Substances 0.000 description 39
239000007864 aqueous solution Substances 0.000 description 37
238000004809 thin layer chromatography Methods 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
238000001665 trituration Methods 0.000 description 32
238000010828 elution Methods 0.000 description 31
235000011054 acetic acid Nutrition 0.000 description 29
229960000583 acetic acid Drugs 0.000 description 29
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
239000011780 sodium chloride Substances 0.000 description 25
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
GNWRWOJMBZGNPL-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-3-trityl-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1CC1C(=O)N(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)S1 GNWRWOJMBZGNPL-UHFFFAOYSA-N 0.000 description 24
238000010992 reflux Methods 0.000 description 24
238000001816 cooling Methods 0.000 description 23
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 21
239000012312 sodium hydride Substances 0.000 description 21
229910000104 sodium hydride Inorganic materials 0.000 description 21
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 20
239000002480 mineral oil Substances 0.000 description 20
235000010446 mineral oil Nutrition 0.000 description 20
238000010438 heat treatment Methods 0.000 description 19
OQJBFFCUFALWQL-UHFFFAOYSA-N n-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
150000001408 amides Chemical class 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000006185 dispersion Substances 0.000 description 15
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150000002430 hydrocarbons Chemical class 0.000 description 15
231100000989 no adverse effect Toxicity 0.000 description 15
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 14
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
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239000002585 base Substances 0.000 description 11
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
150000001298 alcohols Chemical class 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000012280 lithium aluminium hydride Substances 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
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230000037396 body weight Effects 0.000 description 4
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238000002474 experimental method Methods 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
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150000002500 ions Chemical class 0.000 description 4
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238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960000448 lactic acid Drugs 0.000 description 1
JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 1
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
BOKGUZZEEWDHPT-UHFFFAOYSA-N methyl 2-pyrrolo[2,3-b]pyridin-1-ylacetate Chemical compound C1=CN=C2N(CC(=O)OC)C=CC2=C1 BOKGUZZEEWDHPT-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
VBBUFMFZDHLELS-UHFFFAOYSA-N n-(oxomethylidene)carbamoyl chloride Chemical compound ClC(=O)N=C=O VBBUFMFZDHLELS-UHFFFAOYSA-N 0.000 description 1
QJOVPRXBSUNPRO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-3-nitropyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NCC1=CC=C(Cl)C=C1 QJOVPRXBSUNPRO-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000018791 negative regulation of catalytic activity Effects 0.000 description 1
230000009707 neogenesis Effects 0.000 description 1
125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229940116315 oxalic acid Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical group O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
QJIJQNUQORKBKY-UHFFFAOYSA-N piperidin-1-ium;benzoate Chemical compound C1CCNCC1.OC(=O)C1=CC=CC=C1 QJIJQNUQORKBKY-UHFFFAOYSA-N 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
201000009104 prediabetes syndrome Diseases 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
AJXMUHGCDMSUMA-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=C=C[N]1 AJXMUHGCDMSUMA-UHFFFAOYSA-N 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008279 sol Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
JNQNQSCDMKNYEX-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)-2,3-dihydroindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(CO)CC2=C1 JNQNQSCDMKNYEX-UHFFFAOYSA-N 0.000 description 1
YULHWLYTSGKUJG-UHFFFAOYSA-N tert-butyl 2-[[4-[(2,4-dioxo-3-trityl-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,3-dihydroindole-1-carboxylate Chemical compound C1C2=CC=CC=C2N(C(=O)OC(C)(C)C)C1COC(C=C1)=CC=C1CC(C1=O)SC(=O)N1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YULHWLYTSGKUJG-UHFFFAOYSA-N 0.000 description 1
KKFACQDQGPOJSN-UHFFFAOYSA-N tert-butyl-dimethyl-(7h-purin-8-ylmethoxy)silane Chemical compound C1=NC=C2NC(CO[Si](C)(C)C(C)(C)C)=NC2=N1 KKFACQDQGPOJSN-UHFFFAOYSA-N 0.000 description 1
LVOOTRTXPVYOSQ-UHFFFAOYSA-N tert-butyl-dimethyl-[(1-methylimidazo[4,5-c]pyridin-2-yl)methoxy]silane Chemical compound N1=CC=C2N(C)C(CO[Si](C)(C)C(C)(C)C)=NC2=C1 LVOOTRTXPVYOSQ-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
JOQGJRQKCIJIDB-UHFFFAOYSA-N tin;hydrochloride Chemical compound Cl.[Sn] JOQGJRQKCIJIDB-UHFFFAOYSA-N 0.000 description 1
UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Hematology (AREA)
Obesity (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Indole Compounds (AREA)
Heat Sensitive Colour Forming Recording (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA002146701A 1994-04-11 1995-04-10 Composes heterocycliques a activite anti-diabetique, leur preparation et leur usage Abandoned CA2146701A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP6-72083		1994-04-11
JP7208394		1994-04-11

Publications (1)

Publication Number	Publication Date
CA2146701A1 true CA2146701A1 (fr)	1995-10-12

Family

ID=13479165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002146701A Abandoned CA2146701A1 (fr)	1994-04-11	1995-04-10	Composes heterocycliques a activite anti-diabetique, leur preparation et leur usage

Country Status (21)

Country	Link
US (6)	US5624935A (fr)
EP (2)	EP1022274B1 (fr)
KR (1)	KR950032188A (fr)
CN (1)	CN1060173C (fr)
AT (2)	ATE222895T1 (fr)
AU (1)	AU683348B2 (fr)
CA (1)	CA2146701A1 (fr)
CZ (1)	CZ289317B6 (fr)
DE (2)	DE69528000T2 (fr)
DK (2)	DK1022274T3 (fr)
ES (2)	ES2165895T3 (fr)
FI (1)	FI951731L (fr)
HU (1)	HU219887B (fr)
ID (1)	ID20564A (fr)
IL (1)	IL113313A (fr)
NO (2)	NO305987B1 (fr)
NZ (1)	NZ270917A (fr)
PT (2)	PT1022274E (fr)
RU (2)	RU2151145C1 (fr)
TW (2)	TW407156B (fr)
ZA (1)	ZA952990B (fr)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO305987B1 (no) *	1994-04-11	1999-08-30	Sankyo Co	Heterosykliske forbindelser med antidiabetisk aktivitet, deres anvendelse og farmasoeytisk preparat inneholdende disse
TW403748B (en) *	1994-11-02	2000-09-01	Takeda Chemical Industries Ltd	An oxazolidinedione derivative, its production and a pharmaceutical composition for lowering blood sugar and lipid in blood comprising the same
US5925656A (en) *	1995-04-10	1999-07-20	Dr. Reddy's Research Foundation	Compounds having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
CZ293016B6 (cs) *	1995-06-01	2004-01-14	Sankyo Company Limited	Benzimidazolové deriváty a farmaceutické prostředky s jejich obsahem
US5798375A (en) *	1995-07-03	1998-08-25	Sankyo Company, Limited	Treatment of arteriosclerosis and xanthoma
EP0783888A1 (fr) *	1995-12-26	1997-07-16	Sankyo Company Limited	Utilisation de la troglitazone et de thiazolidinediones apparentées dans la fabrication d'un médicament destiné au traitement et la prévention de l'ostéoporose
NZ314406A (en) *	1996-03-18	2000-12-22	Sankyo Co	Treatment or prophylaxis of pancreatitis with a medicament containing an insulin sensitiser including oxazoles and thiazoles
ZA973848B (en) *	1996-05-06	1997-12-02	Reddy Research Foundation	Novel heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them.
US5919782A (en) *	1996-05-06	1999-07-06	Dr. Reddy's Research Foundation	Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
ZA973850B (en) *	1996-05-06	1997-12-02	Reddy Research Foundation	Novel antidiabetic compounds having hypolipidaemic, anti-hypertensive properties, process for their preparation and pharmaceutical compositions containing them.
CA2257284C (fr) *	1996-05-31	2005-10-04	Sankyo Company Limited	Remede pour maladies auto-immunes
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1995
- 1995-04-10 NO NO951398A patent/NO305987B1/no not_active IP Right Cessation
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- 1995-04-10 RU RU95118736/04A patent/RU2151145C1/ru not_active IP Right Cessation
- 1995-04-10 CZ CZ1995910A patent/CZ289317B6/cs not_active IP Right Cessation
- 1995-04-10 RU RU95105423/04A patent/RU2114844C1/ru not_active IP Right Cessation
- 1995-04-10 CA CA002146701A patent/CA2146701A1/fr not_active Abandoned
- 1995-04-11 US US08/419,919 patent/US5624935A/en not_active Expired - Fee Related
- 1995-04-11 ES ES95302409T patent/ES2165895T3/es not_active Expired - Lifetime
- 1995-04-11 DE DE69528000T patent/DE69528000T2/de not_active Expired - Fee Related
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- 1995-04-11 DK DK00102313T patent/DK1022274T3/da active
- 1995-04-11 PT PT00102313T patent/PT1022274E/pt unknown
- 1995-04-11 DK DK95302409T patent/DK0676398T3/da active
- 1995-04-11 KR KR1019950008429A patent/KR950032188A/ko not_active Abandoned
- 1995-04-11 AU AU16383/95A patent/AU683348B2/en not_active Ceased
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- 1995-04-11 ES ES00102313T patent/ES2180477T3/es not_active Expired - Lifetime
1996
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- 1996-11-08 US US08/745,377 patent/US5739345A/en not_active Expired - Fee Related
1997
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1998
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Also Published As

Publication number	Publication date
FI951731A7 (fi)	1995-10-12
EP1022274A1 (fr)	2000-07-26
HUT73765A (en)	1996-09-30
IL113313A (en)	1999-09-22
PT676398E (pt)	2002-03-28
NZ270917A (en)	1996-12-20
CN1060173C (zh)	2001-01-03
EP1022274B1 (fr)	2002-08-28
RU95105423A (ru)	1997-03-20
HK1029338A1 (en)	2001-03-30
ID20564A (id)	1999-01-14
US6117893A (en)	2000-09-12
EP0676398B1 (fr)	2001-10-24
FI951731A0 (fi)	1995-04-11
TW407156B (en)	2000-10-01
NO307299B1 (no)	2000-03-13
US5962470A (en)	1999-10-05
US5739345A (en)	1998-04-14
HU9501040D0 (en)	1995-06-28
ZA952990B (en)	1995-12-21
NO983900L (no)	1995-10-12
AU1638395A (en)	1995-10-19
NO951398L (no)	1995-10-12
DE69523358D1 (de)	2001-11-29
FI951731L (fi)	1995-10-12
NO305987B1 (no)	1999-08-30
NO983900D0 (no)	1998-08-25
RU2114844C1 (ru)	1998-07-10
DE69528000D1 (de)	2002-10-02
ES2165895T3 (es)	2002-04-01
ES2180477T3 (es)	2003-02-16
AU683348B2 (en)	1997-11-06
DK1022274T3 (da)	2002-10-28
RU2151145C1 (ru)	2000-06-20
EP0676398A3 (fr)	1998-07-01
IL113313A0 (en)	1995-07-31
CN1118781A (zh)	1996-03-20
HK1011365A1 (en)	1999-07-09
DK0676398T3 (da)	2001-12-10
ATE207488T1 (de)	2001-11-15
US5624935A (en)	1997-04-29
ATE222895T1 (de)	2002-09-15
US5977365A (en)	1999-11-02
DE69523358T2 (de)	2002-07-11
EP0676398A2 (fr)	1995-10-11
HU219887B (hu)	2001-08-28
NO951398D0 (no)	1995-04-10
TW503237B (en)	2002-09-21
PT1022274E (pt)	2002-11-29
CZ91095A3 (en)	1997-12-17
CZ289317B6 (cs)	2002-01-16
KR950032188A (ko)	1995-12-20
DE69528000T2 (de)	2003-05-28
US5834501A (en)	1998-11-10

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Date	Code	Title	Description
2002-01-22	EEER	Examination request
2004-04-13	FZDE	Discontinued

Publication	Publication Date	Title
CA2146701A1 (fr)	1995-10-12	Composes heterocycliques a activite anti-diabetique, leur preparation et leur usage
CA2177858C (fr)	2010-07-06	Derives du benzimidazole; preparation et utilisation therapeutique
US5578620A (en)	1996-11-26	Thiazolidine and oxazolidine derivatives, their preparation and their medical use
AU737303B2 (en)	2001-08-16	Cyclic amino compounds
TW200827365A (en)	2008-07-01	New spiropiperidine derivatives
US20030078426A1 (en)	2003-04-24	Amine derivative compounds
AU2961599A (en)	1999-10-25	Sulfonamide derivatives
NZ280181A (en)	1996-11-26	Benzylthiazolidinedione and benzyloxazolidinedione derivatives; pharmaceutical compositions
JPH09165371A (ja)	1997-06-24	複素環化合物を含有する医薬
AU700354B2 (en)	1999-01-07	Heterocyclic compounds having anti-diabetic activity, their preparation and their use
AU1053399A (en)	1999-06-07	Pyridylpyrrole derivatives
TW200408628A (en)	2004-06-01	Resorcinol and its derivatives
JPH07330728A (ja)	1995-12-19	複素環化合物
HK1011365B (en)	2002-08-16	Heterocyclic compounds having anti-diabetic activity, their preparation and their use
AU2004207726B2 (en)	2007-03-15	Oligosaccharide derivative
JP2009269850A (ja)	2009-11-19	新規スピロピペリジン誘導体を含有する医薬
JP2001131067A (ja)	2001-05-15	血小板凝集抑制剤又は動脈硬化進展抑制剤